You've Come A Long Way, Baby
by Grid413
Summary: AU - first shot ever at writing fanfiction so please review! Have a good idea where this could go so more to come hopefully. Dean and Sam have finished a tough day hunting but there is never any rest for the good guys, right? M for language. Dean, Sam & OC
1. Chapter 1

**Disclaimer - Dean and Sam aren't mine but the other randoms in this chapter are!**

As Sam dropped the bag with a sigh on to the motel room floor, Dean allowed his body to flop on to the second of two twin beds laid out in front of them. The beds lack of springy comfort meant he did not bounce, or sink in, but instead landed with an unsatisfying thud against the cheap mattress. Sam looked over to his brother lying wide-eyed on the bed, and gathering what little energy he had, shuffled over to his own side of the twins. Picking up the thin pillow, he glanced round to the room's battered looking couch and called out "Shotgun".

"Dude, are you seriously shotgunning the couch?" Dean said to the ceiling.

"It looks a lot more comfortable than either of these beds" replied Sam "And I actually want to get some sort of decent sleep tonight. My legs are killing me"

"Ah Sammy, that's what you get chasing demons round a giant warehouse for two hours" Dean sat up, looking drained and exhausted before breaking out in a smirk "You know you should really work on those chicken legs of yours – hit a few weights, take up a bit of jogging. Might help you take down those bad guys a little faster"

Sam chucked his flimsy pillow at Dean's head before starting to collect up his duvet "You're hardly an Olympic track star yourself. Anyone would have thought you were having an asthma attack after all that running"

"Yeah, yeah, whatever you say Colonel Sanders. How about you get over to your couch and take your crummy pillow with you"

Sam grabbed up his pillow, and dumped both it and the duvet down on the cushions as he set about making up his bed for the night. Dean rubbed at his tired eyes with his hands and looked around the motel room. It had been a long night, and as glad as he was that it was over, the room he and Sam had booked into was far from welcoming. The paper was faded and peeling from the walls, and the room was littered with mismatched furniture. The bed certainly didn't feel up to much either. He considered turning on the ancient TV that sat in the corner, but the effort required far outweighed the desire for a grainy picture and infomercials.

"Well" Dean said as he stood up and stretched out his arms "I ain't getting to sleep in this dump unless I pass out in it. And after the night we've had, I think I deserve that privilege. So, if you need me, I'll be getting drunk in the bar down the street"

"How can you be bothered drinking at this hour?" Sam turned and glanced at his watch "Besides it'll be kicking out time soon"

"Yeah, true, but that just makes it a challenge. The good old-fashioned challenge to get as drunk as possible before they chuck you out"

Sam went back to arranging the couch bed, shaking his head. "You're an idiot Dean. I'm staying here to get some sleep"

"No problem princess" Dean said as he made his way to the door "You stay and get your beauty sleep."

"Try not to get into any trouble"

Dean grinned at Sam "Now, as if I would do that…"

* * *

He came out of the motel car park and pulled up the collar of his coat, feeling a chill wind on the back of his neck. The tiny town in Minnesota where they were staying had little going for it as any sort of tourist attraction, but the gas station and motel provided everything the Winchesters would need. The sky was clear but cold, full of sparkling stars awaiting the first rush of winter snow. Dean started to head towards the flickering lights of the bar he had noticed when they drove into town earlier. The bar appeared to have no name; it was identifiable only by the blinking Budweiser sign attached to the outside. His hands shoved deep in his pockets to protect against the cold, he encouraged his stiff legs down the street, convincing himself that a couple of whiskies would soon have him warm, relaxed and feeling much better.

As Dean got closer, both the sign and the doorway light switched off. "Fuck" he thought, and stopped in his tracks - he had been really, _really_ looking forward to that drink. But before he could turn, the lights both sprung back on again, and a roar of laughter could be heard erupting from within. Dean smiled, and muttered to himself "Sounds like my kinda place". With that, he opened the door and went inside.

What greeted him was not at all what he had expected. The bar was narrow and windowless, with a low ceiling which meant it appeared almost like a tunnel. The dim lighting only added to the effect. A long bar area made up one side of the room while booth seating stretched along the other. It was dull and dank, similar in decor to the motel room he had just left. Yet despite this bar looking like the sort where a man would go to quietly drown his sorrows, the place was, well, _jumping_. Around 30 people were crammed into the small space and every one of them was drunk. Not just drunk, but loud, leery and disinhibited drunk. Dean was shocked to see two male police officers, both still in uniform, swaying and hooting like a pair of over excitable college students. In one of the booths, two middle-aged locals were involved in a pretty serious public display of affection, which Dean thought would have been funny if it hadn't been so grossly blatant that they were enjoying the cackling and encouragement from some of their fellow barflies. Hell, even the barmaid, who had a face that looked like she would be the last person on earth to tolerate this sort of shit, was laughing like a hyena, seemingly just as drunk as her patrons.

Manoeuvring around the drunken antics, Dean managed to squeeze himself into the bar area. After the day he'd had, a drink even in this place would be welcome. But he would have one and leave; no part of him wanted to get drawn into a conversation with an inebriated local.

"'Scuse me?" Dean yelled over the crowd at the barmaid. She turned to face him, gave him a glance over, and smiled.

"And what can I do for you, darlin'?" She said in a rough voice, the kind developed by years of smoking roll ups.

"Just looking for a drink – a decent whiskey if you've got any" replied Dean with a polite smile.

"Well, sugar" the barmaid slurred "You can have your whiskey, but you ain't gonna enjoy yourself as much as we are drinking that. Why don't you have an, appal, appll… an apple juice like the rest of us?"

"A whiskey's fine, thanks"

"Aw come on darlin'! Everyone else here is drinkin' em. And we're havin' a great time!" She whooped as she stumbled backwards into her beer fridges, drawing another round of laughter from the bar.

"Just a Jack thanks" Dean said through a gritted smile. God, what was this he had stumbled into.

The barmaid made a sulky face, but turned and reached to a high shelf above the fridges for the Jack Daniels bottle. She turned back to Dean and clumped the bottle down on the bar top. "Here you go darlin'. Knock yourself out." She paused "Drink it and come back to me when you're a bit more fun". Laughing, she threw Dean a shot glass and went back to the barflies.

"Eh, I don't need the whole bottle sweetheart" Dean called after her, but he was drowned out by more cackling and shouting. Pissed off, he threw some money on the bar and grabbed the bottle by the neck, intending to attempt to find a quiet corner somewhere in this dive to drink.

Scanning the booths at the farthest ends, he suddenly noticed a woman sat tucked away at the back of the bar. She was watching the antics of the drunks, and laughing, while a large tumbler filled with a clear drink sat on the table in front of her. She didn't look as if she was part of the revelry, and although she continued laughing, she didn't look too drunk. She was also pretty hot. Straight red-brown hair fell just past her shoulders, and her skin looked pale cream even under the bars crappy lighting. The tight navy sweater outlined a slim but curvaceous top half, and Dean noticed a pair of knee-high leather boots hanging out the end of the booth where she had laid her legs along the seat. Not bad for a dive bar, Dean thought, not bad at all.

She spotted him checking her out, and waved. Embarrassed for being caught staring but not wanting to look like a coward in front of a hot girl, Dean made his way over to her booth.

"You not invited to the party?" he said, at the same time ramping up his lady-killer smile as he stood over her table.

"No! No, no!" she laughed "I merely got the party started. After that, it was all them!"

Dean wasn't quite sure what she meant by this, but he laughed anyway.

"Do you want a seat?" she asked "It would be nice to have someone to sit and watch the madness unfold with"

"Thanks" said Dean, and he slid into the booth, mirroring her seating position with his legs on the seat so he could see what was going on. He poured himself a shot of whiskey and picked up his glass "Cheers"

"Cheers" the woman replied and picked up her tumbler, taking a large gulp. Whatever was in the glass must have been strong, because she screwed up her face as she lowered the glass and swallowed "Wow. That is like rocket fuel!"

"What are you drinking?" asked Dean

"Appletini – although they didn't have any cocktail glasses in this place so I got it in a tumbler instead. I dread to think how much vodka is in that glass!"

Dean made a face in mock disgust "Appletini?! How the hell did you convince them to serve you that?!"

She laughed again, which made Dean smile. "I actually had to show the lovely hostess how to make it up. Her face was a picture! And they had to drag down this mouldy old bottle of vermouth from the top shelf – it was covered in dust so thick, it was disgusting! But hey, I made it up and let her try it, and soon the whole bar was ordering them!"

She pointed over to the drunks and Dean saw that they all had the same clear drink as the woman did, in a variety of different style glasses as the bar clearly did not cater for the cocktail drinker. How had he not noticed that when he came in? Was he really that tired? He shook his head, rubbed his eyes, and poured himself another shot.

"So what brings you to Minnesota?" the woman asked.

"Business" Dean replied as he went into stock answer mode "What about you?"

"Same". She reached for her glass and took a sip. "What is it you do?"

"Hunting" Dean replied, before realising what he had just said. Where the hell had that come from? "I mean hunting supplies, trade selling, that sort of thing". God he must be tired, blurting out crap like that.

"Ah, I see." The woman didn't seem to have noticed his slip and recovery. "I'm working here freelance. Staying in that awful motel up the road"

"Yeah, the Hilton sure missed a trick not building here" said Dean with a smirk and a glance over at the crowd, who seemed to be trying to convince the barmaid to go into her store room for something.

"So, are you here alone or is there a Mrs Hunting Supplies with you?" the woman enquired with a hint of mischief in her voice.

Excellent thought Dean, I like a woman who gets to the point quickly. Turning on the charm, he raised his eyebrows and looked her straight in the eyes "No. There's no Mrs Hunting Supplies – just me and my brother Sam. All alone in that crappy motel, and you, you're all alone too?"

"Hmm, yeah all alone" she giggled back "Well, I have a brother too but he isn't around here at the moment"

"So, he's not here to kick my ass if I continue getting drunk with his sister?"

"Nope, guess not. Although I will warn you, I can be very badly behaved when liquor is involved"

Jackpot. Dean mentally high-fived with himself and smiled.

"Well then, we best get you some more liquor" he said, sliding out of the booth and noticing that the barmaid was stumbling out a back room with what appeared to be some sort of sound equipment. "What are you having?"

"Just another appletini" replied the woman casually "And get one for yourself – trust me, you'll love them!"


	2. Chapter 2

Sam awoke just as his right leg went into cramp, and it was a bad one. The pins and needles sensation rapidly stiffened his calf, and he found himself lurching up off the couch in an attempt to stop the pain spreading any further. He hobbled around in the dark as his leg spasmed, silently swearing under his breath as the blood rushed to his muscle. He lapped back and forth around the outsides of the two twin beds, and by the third loop the pain had begun to wear off. Sam slumped back down on the couch and rubbed at his lower leg, feeling the muscle finally start to relax.

Knowing a pain killer would help to ease things, Sam wondered if he could get away with turning the light on to look for his supplies in his bag. The room was pitch dark as minimal light was managing to break through the curtains. Dean was probably drunk and wouldn't notice he thought. He must be pretty well passed out if he failed to hear Sam crashing about just then. Usually even the slightest noise from Sam resulted in a barrage of abuse from Dean, but he hadn't even stirred when he was hopping about the motel room. Deciding to risk the wrath as the pain in his leg started to dull, Sam reached over to turn on the small light on the table.

The panic immediately set in as Sam realised that Dean was not in his bed. It hadn't been touched since he had landed on it earlier that evening, with the covers still in a vaguely Dean shaped ruffle. His mind now far from thinking about painkillers, Sam firstly checked the side of each bed and then checked in the small bathroom. No Dean. Sam glanced at his watch - 4.47am. Where the hell was he?

* * *

Having shoved on a pair of jeans, a jumper and his boots, Sam grabbed his coat and made his way out of the motel door. The cold night air blew at him as he made his way across the car park, where he quickly scanned the inside of the Impala in case Dean had decided to sleep in there. Not finding him inside, Sam made his way to the road and he glanced up and down, looking for any sign of his missing brother.

The only light he could see was the flickering red Budweiser sign. If he is lying drunk in an alley off this road, I will kill him, thought Sam and he broke into a slow jog towards the bar, scanning down side streets and in doorways in case he spotted Dean slumped in one of them. As he got closer, he could have sworn he heard music coming from the building, but surely they couldn't have a late license – till 5am? Plus there was a cop car parked across the street, although no sign of any cops in it. There is no way they would get away with a lock in past the legal license time.

But as he slowed his jog outside, Sam was certain there was music coming from the bar. In fact a full blown party seemed to be taking place inside, with someone singing to a riot of encouragement. From outside the bar Sam could tell they were terrible, whoever this poor soul was. They sounded like a cat being strangled, or worse a demon, such was the wreck they were making of the high notes. Whatever the case, Sam thought it would be unlikely that Dean was still here. But it would be worth finding out if he had been in the bar, and Sam hoped he had, as it would be a real problem if he hadn't.

* * *

If Dean had been shocked when entering the bar, then Sam was stunned to his very core. Surrounded by a rabble of drunken locals, including the two cops missing from their squad car, was Dean. Not just Dean, but Dean topless, standing on a table singing with all his heart into a karaoke machine's microphone. Sam could only watch open mouthed as his brother, who he thought he knew like the back of his hand, belted out the lyrics to 'Toxic' by Britney Spears with what looked like a cloth napkin, or maybe a dish towel, tied around his head like a bandana. As the musical interlude played through an ancient sound system, Dean then sent a small group of drunken middle aged woman into a frenzy as he shook his ass like a stripper, and much to Sam's surprise, the male members of the crowd just shouted more encouragement. Sam had never seen Dean sing karaoke, something that Dean had categorically stated on a number of occasions that he would never, ever, ever, do. Hell, Dean had even once told him he would rather wrestle another hellhound than stand up and make a fool of himself singing like some TV talent show asshole.

The music slowly died out, and Dean jumped off the table to an extended round of applause, whoops and one older woman not so subtly pinching his butt. As the barflies patted him on his back and handed him another glass of what looked like straight vodka, he spotted Sam standing in the doorway.

"Sammy!" Dean yelled as he stumbled towards him "Did you see me up there? I was on freaking fire, man!"

"Eh, yeah" Sam replied, wincing as Dean threw his head back and downed his drink in one swift gulp "Are you planning to stay much longer? It's after 5am"

"Really? God feels like I've been here for all of 5 minutes!" Swaying, Dean steadied himself on the edge of the bar "Ok. Just let me find my shirt. I think Winston won it from me… playing shots, or, something, I can't remember."

Dean stumbled his way through the crowd towards a guy who appeared to be wearing two shirts, and Sam began looking through a large pile of coats for his jacket. It was then that an attractive woman approached him from his left and tapped Sam's shoulder.

"I think this might be his" she smiled, holding out Dean's leather jacket in her hand "He was sitting up at the back of the bar with me before the urge to entertain took him on to the top of the tables"

Sam thanked her, mentally cursing that only his brother would be lucky enough to find a good looking girl to sit with in a Minnesota dive bar at 5am. "Do you know how he ended up so wasted?"

"Yeah, I'm afraid the whole bar has been necking appletini's all night thanks to yours truly! Even your brother managed to get over his macho man-drinking and have a few!" she laughed, before lowering her voice to a whisper "He doesn't really handle his cocktails that well"

"To be honest, he's not a cocktail drinker" Sam replied, convinced now that Dean's drink had been spiked, or that he had been drinking some local backwater moonshine. Noting the woman's smile and relaxed manner, it dawned on Sam that she wasn't drunk. At least not anything like the rest of the bar patrons, who continued with their loud and lewd behaviour.

"Anyway, I think its time for me to hit the road too" she stated "You must be Sam, right? He told me that you were both staying at the motel up the street? I'm staying there too so I'll help you get our star performer back safely"

Sam smiled "I sure we'll manage, thanks, but we will walk up with you to make sure you get back ok. I'm sorry; I never caught your name?"

"Ah" the woman extended her hand, which Sam took "How rude of me! I'm E…"

Dean interrupted "Winston wasn't for giving me back my shirt, so I hit him to teach him some manners. Wha… what an asshole. Let's go Sammy. You too sweet cheeks", and he linked his arms over both their shoulders.

"Eh, Dean?" started Sam, but the drunken locals hadn't take too kindly to Dean knocking out one of their friends, and seemed to be shuffling round in an edgy manner. Wanting to avoid a fight, Sam looked at the woman, who could only stifle a laugh as Dean hung on to them. "Yeah, let's go" and they hustled a shirtless Dean outside.

**More to come soon!**


End file.
